Long-Wavelength, Photostable, Two-Photon Excitable BODIPY Fluorophores Readily Modifiable for Molecular Probes

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• 作者：Xinfu Zhang ; Yi Xiao ; Jing Qi ; Junle Qu ; Bosung Kim ; Xiling Yue ; Kevin D. Belfield
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：September 20, 2013
• 年：2013
• 卷：78
• 期：18
• 页码：9153-9160
• 全文大小：480K
• 年卷期：v.78,no.18(September 20, 2013)
• ISSN：1520-6904

文摘

Near-infrared (NIR) fluorescent probes are increasingly popular in biological imaging and sensing, as long-wavelength (650鈥?00 nm) excitation and emission have the advantages of minimum photodamage, deep tissue penetration, and minimum interference from autofluorescence in living systems. Here, a series of long-wavelength BODIPY dyes SPC, DC-SPC, DPC, and DC-DPC are synthesized conveniently and efficiently. They exhibit excellent photophysical properties in far red to near-infrared region, including large extinction coefficients, high fluorescence quantum yields, good photostability, and reasonable two-photon absorption cross section. Comparison of single-molecular imaging confirms that DPC is a much more efficient and more photostable NIR fluorophore than the commonly used Cy5. Also importantly, two kinds of convenient functionalization sites have been reserved: the aryl iodide for organometallic couplings and the terminal alkyne groups for click reactions. Further derivatives DC-SPC-PPh3 exhibit specificity to localize in mitochondria. The introduction of triphenylphosphonium (TPP) moieties mediates its hydrophilic鈥搇ipophilic balance and makes DC-SPC-PPh3 appropriate for cell labeling. Their long-wavelength emission at 650 nm can efficiently avoid the spectral crosstalk with other probes emitting in the visible light region. Superior photostability, low cytotoxicity, and two-photon excitable properties demonstrate its utility as a standard colocalizing agent to estimate the other probes鈥?local distribution.